Historic Route 66 2024 Holidays

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Top Flight + Hotel Deals in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
per person
5 Aug - 10 Aug
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,001 reviews)
Staff very friendly and helpful. Rooms were good. No coffee makers in rooms which is a bit different but each morning complimemtary coffee was available in the lobby. Really good location for us and we would highly reccommend.

Reviewed on 14 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
5 Aug - 10 Aug
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on 13 May 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
5 Aug - 10 Aug
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Location was fantastic and the property is beautiful!

Reviewed on 15 May 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
5 Aug - 10 Aug
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (679 reviews)
Enjoyed our stay at the Pendry. It is in a great location and very walkable. Housekeeping was great. Enjoyed the restaurant and bar and the staff was very friendly.

Reviewed on 15 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
5 Aug - 10 Aug
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Where to stay in Historic Route 66

Find the best Historic Route 66 areas and neighborhoods for the activities you enjoy most. Learn more about Historic Route 66
Downtown Chicago featuring a city

Downtown Chicago

1 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Historic Route 66

Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €156 per night from 27 May to 28 May
€156
per night
27 May - 28 May
8.4/10 Very Good! (3,056 reviews)
"Love this property and location!"

Reviewed on 11 May 2024

Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel
Central Loop Hotel
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €156 per night from 27 May to 28 May
€156
per night
27 May - 28 May
8.4/10 Very Good! (1,630 reviews)
"Lovely room in a fantastic neighborhood right in the thick of it. Surprisingly and delightfully affordable. Folks payin' 3-4X as much as the W just a block away."

Reviewed on 13 May 2024

Central Loop Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is €161 per night from 27 May to 28 May
€161
per night
27 May - 28 May
7.6/10 Good! (6,725 reviews)
"fast elevator"

Reviewed on 14 May 2024

Congress Plaza Hotel
See all 18,972 properties in Historic Route 66
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Historic Route 66 holiday package cost?
Our Historic Route 66 packages, which start at just €1,165, are an easy way to save big bucks. Pick your preferred flights, hotels and rental cars to create your ideal trip.
How do I get a cheap travel package to Historic Route 66?
Book everything all in one place with our Historic Route 66 holiday packages. We have incredible bargains on hotels, flights and more that’ll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 properties globally to select from, you’ll have the flexibility to mix and match as you please.
What are the top hotels in Historic Route 66?
If you’re headed to Gillespie, you can’t go past Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton. Both are excellent bases for exploring this lively Historic Route 66 city.
How far in advance should I book my Historic Route 66 holiday?
The earlier you book, the better. Airlines usually release flight tickets nearly 12 months prior to departure, and this is a fantastic opportunity to pick up some of the lowest prices. Just been told you need to take your holiday time next month? That’s alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Historic Route 66 travel package include?
You can select from a combination of hotels, flights and rental cars. Once you’ve made your booking, you can add the fun stuff like activities and experiences. Want to pick your fare class? That’s possible too. The choice is all yours when it comes to crafting your dream Historic Route 66 getaway.
What should I know before booking a Historic Route 66 travel package?
An Expedia travel package can be tailored to your budget and is a fantastic way to make your hard-earned dollars stretch further. How little or much you include is totally up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with a Historic Route 66 Expedia holiday package?
Yes, definitely. Expedia has more than 550 airline partners to pick from around the globe. With such a big range of choice, finding the perfect carrier to take you to Historic Route 66 shouldn’t be hard.
If I'm not able to travel, can I cancel my Historic Route 66 holiday package?
You sure can, and we’re here to help. You may be able to cancel or change your Historic Route 66 holiday package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your holiday, take a look at our Customer Service Portal for more information.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.